Top Beach vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Beachside

Nantucket Town

per person

Sep 18 - Sep 20

found 1 day ago

Roundtrip flight included

Columbus (CMH) to Boston (BOS)

9.4/10 Exceptional! (156 reviews)

Really good stay, the kids loved all the activities like the arcade, pool, evening movies and popcorn etc...

Reviewed on Aug 12, 2025

The Mansion at Ocean Edge

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip flight included

Springfield (SGF) to Boston (BOS)

8.2/10 Very Good! (1,001 reviews)

Everything was great!

Reviewed on Aug 13, 2025

Harbor View Hotel

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

The Harbor View Hotel is exactly what holiday dreams are made of. The property is absolutely stunning, beautifully maintained with breathtaking views and elegant charm throughout. From the moment we arrived, the staff went above and beyond. Everyone was warm, attentive, and incredibly polite, making us feel truly welcomed. The entire hotel smells amazing, like a luxury spa. Our room was spacious, beautifully decorated, and spotlessly clean. Did I mention how gorgeous the entire property is? Our trip to Martha’s Vineyard wouldn’t have been half as magical without this hotel. It was truly the highlight of our stay. This is hands down the place to stay when visiting the Vineyard. I already can’t wait to return!

Reviewed on Jun 26, 2025

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5* Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

The Harbor View Hotel is exactly what holiday dreams are made of. The property is absolutely stunning, beautifully maintained with breathtaking views and elegant charm throughout. From the moment we arrived, the staff went above and beyond. Everyone was warm, attentive, and incredibly polite, making us feel truly welcomed. The entire hotel smells amazing, like a luxury spa. Our room was spacious, beautifully decorated, and spotlessly clean. Did I mention how gorgeous the entire property is? Our trip to Martha’s Vineyard wouldn’t have been half as magical without this hotel. It was truly the highlight of our stay. This is hands down the place to stay when visiting the Vineyard. I already can’t wait to return!

Reviewed on Jun 26, 2025

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3 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Mansion at Ocean Edge

Save 100% on your flight

per person

Sep 25 - Sep 28

found 10 hours ago

Roundtrip flight included

Philadelphia (PHL) to Boston (BOS)

8.2/10 Very Good! (1,001 reviews)

Everything was great!

Reviewed on Aug 13, 2025

Harbor View Hotel

Save 100% on your flight

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

The Harbor View Hotel is exactly what holiday dreams are made of. The property is absolutely stunning, beautifully maintained with breathtaking views and elegant charm throughout. From the moment we arrived, the staff went above and beyond. Everyone was warm, attentive, and incredibly polite, making us feel truly welcomed. The entire hotel smells amazing, like a luxury spa. Our room was spacious, beautifully decorated, and spotlessly clean. Did I mention how gorgeous the entire property is? Our trip to Martha’s Vineyard wouldn’t have been half as magical without this hotel. It was truly the highlight of our stay. This is hands down the place to stay when visiting the Vineyard. I already can’t wait to return!

Reviewed on Jun 26, 2025

The Beachside

Nantucket Town

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Boston (BOS)

9.4/10 Exceptional! (156 reviews)

Really good stay, the kids loved all the activities like the arcade, pool, evening movies and popcorn etc...

Reviewed on Aug 12, 2025

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See all available trips from Columbus to Eastern Massachusetts

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4 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Nantasket Beach Resort

Nantasket Beach

Save 100% on your flight

per person

Sep 24 - Sep 28

found 18 hours ago

Roundtrip non-stop flight included

Seattle (SEA) to Boston (BOS)

8.6/10 Excellent! (1,011 reviews)

Beautiful view, good location

Reviewed on Aug 18, 2025

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Boston (BOS)

9.4/10 Exceptional! (174 reviews)

The location was awesome. Right on the beach. Room was clean and bathroom was clean good shower and water pressure. Breakfast was delicious and staff super friendly and polite.

Reviewed on Aug 9, 2025

The Mansion at Ocean Edge

Save 100% on your flight

per person

Sep 18 - Sep 22

found 1 day ago

Roundtrip non-stop flight included

Omaha (OMA) to Boston (BOS)

8.2/10 Very Good! (1,001 reviews)

Everything was great!

Reviewed on Aug 13, 2025

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How do I book the best Eastern Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Eastern Massachusetts beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Eastern Massachusetts?

A rental steps from the shore creates an amazingly affordable Eastern Massachusetts beach vacation. Seaside sojourns during low season start from $802. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Eastern Massachusetts?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Eastern Massachusetts beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Eastern Massachusetts vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Eastern Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Eastern Massachusetts beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Eastern Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Eastern Massachusetts tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Eastern Massachusetts beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Eastern Massachusetts. (OK, maybe not that last part.)

Top Beach Eastern Massachusetts Hotels

Colonial Acres Resort

114 Standish Way, West Yarmouth, MA

2 hours drive from Fenway Park

You will love your stay at this hotel and walk along the waves in West Yarmouth, as you'll be a short walk from Cape Cod Beaches. An indoor pool and a hot tub ...

Travelers like: close to beach, indoor pool

Travelers say...

"Ocean view as advertised and only a short walk from the beach and nice restaurant"

Reviewed on Sep 1, 2024

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

2 hours drive from Fenway Park

At this hotel, get ready to lounge by the shoreline in West Yarmouth, as you'll be a short walk from Cape Cod Beaches. Amenities at Bayside Resort Hotel include ...

8.6/10 Excellent! (1,471 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"Nice hotel"

Reviewed on Aug 16, 2025

Aloft by Marriott, Boston Seaport District

401-403 D Street, Boston, MA

7 min walk from Fenway Park

At this hotel, get ready to lounge by the shoreline in Boston, as you'll be close to the beach. Amenities at Aloft by Marriott, Boston Seaport District include ...

8.8/10 Excellent! (1,323 reviews)

Travelers like: close to beach, indoor pool

Travelers say...

"The housekeeping staff was wonderful! We were disappointed that the pool was out of service during the entirety of our stay. Overall, very nice facility!"

Reviewed on Aug 7, 2025

See all 15,772 properties in Eastern Massachusetts

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.